My son is just about a year older than yours, so I just got through it all not too long ago. We had a potty chair, but never any interest. He turned 3 in February, and still no real interest, sitting or standing. I took my week of vacation in March, and we hit it real hard. I took off the diapers and NO PULL UPS, they're the same as a diaper to them. We did big boy underwear. I started Monday morning, and by Wednesday, we actually left the house in underwear and came home clean!! He did not want the embarassment of an accident in public, which worked great for me. I had him stand, like daddy, and that worked best. I really had to stay on him about going, because he would hold it for hours on end. After this first week, I took him Walmart on Saturday and let him pick out 2 more packs of his favorite big boy underwear. We had an accident or 2 every day for the first few weeks, but if you catch a little tinkle, run them to the bathroom and have them finish in the potty if possible. Okay, so that was peeing, but #2 was a whole new battle. He was scared to death to sit on the potty and he said it hurt to poop, so for those first few weeks I let him have a pull up on at night, and he would poop then. It took almost 2 months longer to get him to go poop in the potty, but we were finally successful and stopped buying diapers and pull ups completely in June. They need to do it in thier own time, to an extent, but if you do not give them a little push, I'm convinced boys would wear diaper thier whole lives!! If you put him in underwear and he still has huge messes all day, he is probably not quite ready, but the biggest clue for me was that my son started waking up dry in the mornings, and that's when I knew he had definitely gained his bladder control. Sorry this is so long, I hope it helps. You will do fine, and so will your little guy!!